Chen Andrew D, Herbort James H, Wappes Ethan A, Nakafuku Kohki M, Mustafa Darsheed N, Nagib David A
Department of Chemistry and Biochemistry, The Ohio State University Columbus OH 43210 USA
Chem Sci. 2020 Jan 31;11(9):2479-2486. doi: 10.1039/c9sc06239d.
A radical cascade strategy for the modular synthesis of five-membered heteroarenes ( oxazoles, imidazoles) from feedstock reagents ( alcohols, amines, nitriles) has been developed. This double C-H oxidation is enabled by generated imidate and acyloxy radicals, which afford regio- and chemo-selective β C-H bis-functionalization. The broad synthetic utility of this tandem hydrogen atom transfer (HAT) approach to access azoles is included, along with experiments and computations that provide insight into the selectivity and mechanism of both HAT events.
已开发出一种从原料试剂（醇、胺、腈）模块化合成五元杂芳烃（恶唑、咪唑）的自由基串联策略。这种双C-H氧化是由生成的亚氨酸酯和酰氧基自由基实现的，它们提供区域和化学选择性的β C-H双官能化。包括这种串联氢原子转移（HAT）方法用于合成唑类的广泛合成效用，以及提供对两个HAT事件的选择性和机理深入了解的实验和计算。
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